And my boss is doing a new thing which is very hurtful to me. He seems to want to extend the day for me as long as possible. So my "end time" is 5:00 PM. And I try to leave around 4:50 just to make the train. But I still have my phone with email so there is almost nothing I can't do with that for the 10 minutes that I would be gone.

First, he started with this... we get work to do all through the day, at 9 am, 1 pm, 3 pm and ever single one of them he sets up for execution at 4:30, 4:45, and 5. (and execution takes a few minutes) so I absolutely will miss my train. And what you have to know is that the trains are so bad that if you miss the first one, they get delayed. So if you go for the second at rush hour it could be 10 minutes late. And beyond that.. there are no more seats at the station anymore because the homeless sleep there so if the train is late... get stand for the 30 minutes or so I am at the station.

Second, there is one thing I can't do from the phone, that is put these packages on the shared drive. Also, no one else can do that because it is limited to people who have access. Now, he keeps demanding that anything that people want to do after hours be put on the drive. EVEN THOUGH HE CAN DO THAT.

IMHO, a clear sign that he is trying to keep me late. The rule is, and has always been that I work during "regular business hours" but our "customers" refuse to do that. He gets paid 3X what I do, so, if something comes in outside of regular business hours, he has to deal with it himself -- but he is always trying to push me to spend my night dealing with it, even though it doesn't help him at all.

My friend says I should talk to him about but I can't. First, after 20+ years of bosses doing this exact same thing to me, it is hurtful and demeaning in a way that I don't think I could have a conversation without crying. And second, I have lost faith that if he is doing this -- that it isn't on purpose. How could I believe otherwise? I have worked with him for years and every year more demeaning work comes my way.

I fear our relationship is falling into passive agressive games like my last boss, but I don't really know how to stop it. I don't trust that talking to him would do anything but make him angry. All of the people he works with do this too. And all of their employees stay late. I have tried to get them not to but they all do.